WO2016111661A1 - Technique de formulation de capsule pour le pyriproxyfène, un analogue d'hormone juvénile utilisé comme régulateur de croissance d'insectes - Google Patents

Technique de formulation de capsule pour le pyriproxyfène, un analogue d'hormone juvénile utilisé comme régulateur de croissance d'insectes Download PDF

Info

Publication number
WO2016111661A1
WO2016111661A1 PCT/TR2016/000003 TR2016000003W WO2016111661A1 WO 2016111661 A1 WO2016111661 A1 WO 2016111661A1 TR 2016000003 W TR2016000003 W TR 2016000003W WO 2016111661 A1 WO2016111661 A1 WO 2016111661A1
Authority
WO
WIPO (PCT)
Prior art keywords
formulation according
reactant
weight
pyriproxyfen
formulation
Prior art date
Application number
PCT/TR2016/000003
Other languages
English (en)
Inventor
Yildiztekin TUNCAY
Original Assignee
Entovest İlaç Κi̇μυα Ve Teknoloji̇ Araştirma Merkezi Sanayi̇ Ti̇caret Li̇mi̇ted Şi̇rketi̇
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Entovest İlaç Κi̇μυα Ve Teknoloji̇ Araştirma Merkezi Sanayi̇ Ti̇caret Li̇mi̇ted Şi̇rketi̇ filed Critical Entovest İlaç Κi̇μυα Ve Teknoloji̇ Araştirma Merkezi Sanayi̇ Ti̇caret Li̇mi̇ted Şi̇rketi̇
Publication of WO2016111661A1 publication Critical patent/WO2016111661A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings

Definitions

  • the invention relates to the manufacture of the capsule formulation of pyriproxyfen molecule for use in the plant protection, the control of mosquito/housefly larvae and the control of insect pests in the veterinary hygiene and to the use thereof for the mentioned purpose.
  • prolonged action is obtained and the three (3) generations of the insect pests are taken under control with a single application.
  • the invention relates to the action that lasts at least 2-3 times longer than the other previous formulations (EW, EC, WDG, G) owing to the novel capsulation formulation of pyriproxyfen, which is used against the agricultural pests (larvae and nymphs) and the larvae of mosquito and housefly.
  • the capsules of pyriproxyfen according to the invention have been observed to be effective also on the insect pest eggs, in addition to the larvae and nymphs.
  • the invention also relates to the use of the CS type in the control of the nymphs of flea and cockroach within the context of public health.
  • the capsulation manufacturing technique and the superior efficacy obtained with this formula are also within the scope of the invention.
  • the liquid formulations include Simple Solutions (Water Soluble Concentrates (SL), Solutions for Use in the Seed Dressing (LS), Liquid Formulations Dissolved in Oil (OL), Ultra Low Volume Liquids (UL), Dispersible Solutions (Emulsifiable Concentrates (EC), Dispersible Concentrates (DC), Emulsions (Emulsions (oil in water) (EW), Emulsions for Use in the Seed Dressing (ES), Micro-emulsions (ME), Suspensions (Aqueous Suspension Concentrates (SC), Suspension Concentrates Applied to Seeds (FS), Suspension Concentrates of Oil Origin (OD), Aqueous Suspo-emulsions (SE) and Dual Character Formulations.
  • Simple Solutions Water Soluble Concentrates (SL), Solutions for Use in the Seed Dressing (LS), Liquid Formulations Dissolved in Oil (OL), Ultra Low Volume Liquids (UL), Dispersible Solutions (Emulsifiable Concentrates (EC), Dispersible Concentrates (DC), Emul
  • Solid formulations are classified as Directly Used Solid Formulations (Powder preparations (DP), Powders for Dry Application to the Seeds (DS), Granules (GR), Directly Used Tablets (DT), Solid Formulations used after Dispersion in Water (Wettable Powders (WP), Dispersible Powders for Use in the Seed Dressing (WS), Water Dispersible Granules (WG), Water Dispersible Tablets (WT), Emulsifiable Granules (EG), Emulsifiable Powders (EP), Solid Formulations used after Dissolution in Water (Water-Soluble Powders (SP), Water Soluble Powders for use in the Seed Dressing (WS), Water Soluble Granules (SG) and Water Soluble Tablets (ST)).
  • DP Directly Used Solid Formulations
  • DP Powders for Dry Application to the Seeds
  • GS Granules
  • Directly Used Tablets Solid Formulations used after Dispersion in Water (WP), Dispersible Powders for Use in the Seed Dressing (WS), Water
  • the pesticide manufacturers always search the ways for developing and formulating the pesticides in a way that is safer for the environment, humans and other non-targeted organisms, or they receive the support from the academic institutions in this regard.
  • the increasing environmental consciousness and the research conducted about the harmful effects of the chemicals have accelerated these efforts even further.
  • the harmful effects of the pesticides on the one hand and the health risks and economic losses caused by the insect pests on the other hand prompted the researches to seek a safer and more effective pesticide.
  • the emulsion concentrate (EC) and oil in water emulsion (EW) formulations of pyriproxyfen are used for the protection of plants.
  • the formulation types of Emulsion Concentrate (EC), Suspension Concentrate (SC), Granule (Gr) and Water Dispersible Granule (WDG) are used.
  • EC Emulsion Concentrate
  • SC Suspension Concentrate
  • Gr Granule
  • WDG Water Dispersible Granule
  • SC, EC, WDG, Gr and EW formulation types lead to many undesirable results such as the irritation and the harmful effects of the auxiliary substances.
  • Emulsion Concentrate EC
  • Oil in Water Formulation Oil in Water Emulsion-EW
  • Granule G
  • Water Dispersible Granule WG, WDG
  • Capsule Suspension CS
  • pyriproxyfen pyriproxyfen
  • invention no. CN 101379982 B entitled "Insecticidal composition containing pyriproxyfen and avermectin" relates to a composition belonging to the technical field of pesticides and comprising pyriproxyfen and abamectin and synergy.
  • the invention no. CN 103385251 A entitled "Insecticidal composition comprising pyriproxyfen” is an insecticidal composition comprising pyriproxyfen.
  • Said invention provides synergic effect against various pests that damage the agricultural products. By means of the composition, the pesticide dose is reduced, the pesticide dose on the plants is reduced and the environmental pollution is reduced.
  • the object of the invention obtained based on the mentioned state of the art is to enable the formulation of pyriproxyfen molecule, which is used for the control of insect pests in the plant protection, public health (control of mosquito-housefly larvae) and the animal health, by means of the capsulation (CS, MC) technique being safer for the human and other non-targeted organisms, reducing/eliminating the problem of residue in the foods and the crops and providing prolonged action.
  • Another object of the invention is to develop a novel formulation technique capable of controlling minimum 3 generations by means of a single application. This provides the possibility of both preventing the contamination of the environment and the products owing to the smaller amount of chemical used and of developing a control program with lower cost.
  • Another object of the invention is to achieve the control of the new resistant nymphs, which will hatch after the application of the pesticide, before they reach the mature state, owing to the insect growth regulator (IGR) active agents.
  • IGR insect growth regulator
  • Another object of the invention is to prevent the labor losses by reducing the number of pesticide applications. Another object of the invention is to obtain a safer formulation with the water-based capsulation instead of the hazardous solvents and other auxiliary substances in the conventional formulations.
  • Another object of the invention is to provide a solution for the inability to achieve uninterrupted control between the generations, which is a problem of the prior art. Owing to the long term control provided by the capsulation technique, the uninterrupted control of the insect pests becomes possible.
  • Active agent is protected from the sun rays by the polymer shell.
  • the pesticide composition is developed, which is described below with all the details and alternative embodiments.
  • This composition is used for the control of pests in many fields, notably the agricultural pests.
  • the invention provides a capsule formulation of pyriproxyfen molecule for use in the control of insect pests in the plant protection, public health and animal health, comprising pyriproxyfen, emulsifier mixture, solvent, antimicrobial preservative agent, anti-foam agent, anti-freeze agent, reactant 1 , reactant 2, reactant 3, thickener and vehicle, wherein said formulation is safer for the human and other non-targeted organisms, reduces/eliminates the problem of residue in the foods and the crops and provides prolonged action.
  • the invention also provides a capsulation (CS, MC) method for said formulation comprising the process steps of mixing pyriproxyfen, solvent and capsule reactant 1 to prepare an emulsifiable pyriproxyfen solution, adding emulsifier mixture, antifreeze agent, antimicrobial preservative agent and anti-foam agent into the water to prepare the water phase of the emulsion, emulsifying the prepared pyriproxyfen solution in the water phase with the aid of a high-speed mixer, slowly adding the other reactants, i.e. reactant 2 and reactant 3, into the emulsion formed, resting the mixture in order to terminate the initiated polymerization reaction and then adjusting the viscosity with the aid of the thickener.
  • CS, MC capsulation
  • the invention relates to the use of pyriproxyfen with the capsule suspension (CS) formulation type for the control of the pests in the plant protection (pests mentioned in the following table) and the public health (control of the mosquito and housefly larvae).
  • CS capsule suspension
  • the technique for manufacturing the pesticide composition according to the invention is similar to the capsulation technique applications for the other pesticide molecules.
  • the primary feature is the ability to obtain more effective result in the pest control, owing to the capsulation of the pyriproxyfen molecule.
  • the capsulation form of pyriproxyfen was never tried in the plant protection, public health and animal health. Table.1. Agricultural Pests:
  • the manufacturing technique for the formulation with given contents by percentage comprises the following process steps:
  • the emulsifier mixture mentioned in the table may be a combination of more than one emulsifier or may comprise a single emulsifier. These emulsifiers may belong to ionic, anionic and nonionic group or may be a combination of these groups.
  • the emulsifiers able to be used in the product include amine ethoxylates, EO/PO block polymers, ether sulfates, saturated alcohol alkoxylates, saturated alcohol ethoxylates, sorbitan ester ethoxylates, tributylphenol ethoxylates, phosphate esters, tristryl phenol ethoxylates, sulfonation products, polycondensation products, nonyl phenol ethoxylates, alkyl benzene sulfonates, castor oil ethoxylates, EO/PO alkoxylation products, saturated alcohol ethoxylates, olein sulfonates and sulfosuccinate groups, which may be used alone or in combinations according to different proportions.
  • a 1/1 mixture of tristryl phenol ethoxylate and nonyl phenol ethoxylate groups is preferably used.
  • the solvent mentioned in the table is the liquid medium, in which the normally solid active agent pyriproxyfen is dissolved. Since the invention is realized with the interfacial polymerization technique, it may be formulated using only the water- insoluble solvents.
  • the hydrocarbons such as xylene, benzene, toluene, cyclohexane, solvesso 100, solvesso 150, solvesso 200 and exxsol series as well as the vegetable oils obtained from oily seeds, their ethyl and methyl esters and the terpenes of vegetable origin are encompassed by the invention.
  • a combination of more than one solvent may also be used.
  • the xylene solvent is preferably used.
  • the anti-freeze agent mentioned in the table comprises the glycol derivatives that prevent the freezing at low temperatures as a known practice in the water-based pesticide formulations. These additives are ethylene glycol, monopropylene glycol, dipropylene glycol, diethylene glycol and glycerin. In the formulation, monopropylene glycol is preferably used.
  • the reactant 1 mentioned in the table refers to the organic compounds that contain isocyanate functional group.
  • the function of the reactant 1 in the formulation is to polymerize on the emulsion droplets-water interface and form a polyurea capsule wall with the aid of catalyst solution following the formation of emulsion by way of addition thereof into the prepared pyriproxyfen oil phase.
  • These compounds may be methyl isocyanate, methylene diphenyl diisocyanate (MDI), hexamethylene diisocyanate (HDI), toluene diisocyanate (TDI), naphthalene diisocyanate (NDI), methylene bicyclohexyl isocyanate (HMDI) or isophorone diisocyanate (IPDI).
  • MDI methylene diphenyl diisocyanate
  • HDI hexamethylene diisocyanate
  • TDI toluene diisocyanate
  • NDI naphthalene diisocyanate
  • HMDI methylene bicyclohexyl isocyanate
  • IPDI isophorone diisocyanate
  • Reactant 2 and reactant 3 mentioned in the table are amines that form a polyurea capsule shell by undergoing polymerization reaction with the reactant 1 , i.e. the isocyanate group.
  • a premix of reactant 2 and reactant 3 is formed in water to prepare the catalyst solution.
  • the prepared catalyst solution is slowly added on the pyriproxyfen oil phase emulsified in water, thereby initiating the reaction for the formation of the polyurea capsule shell.
  • Amines used in the synthesis of the polyurea capsule shell may belong to the primary, secondary or tertiary amine groups.
  • Said amines include ethylamine, ethylene diamine, diethylene triamine, triethylene tetraamine, dimethylamine, trimethylamine, diethylamine, diisopropylamine, dimethylaminopropylamine and triisopropylamine.
  • the thickener mentioned in the table refers to the additives able to be used for adjusting the viscosity of the formulation after the polymerization reaction terminates. These include xanthan gum, guar gum, gum arabic, carboxymethyl cellulose, methyl cellulose, hydroxypropyl cellulose. In the formulation, xanthan gum is preferably used.
  • the vehicle mentioned in the table is water and the anti-foam agent and the antimicrobial preservative agent are the products frequently used in the pesticide formulations.
  • a silicone-based anti-foam agent is preferably used in the formulation.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne l'action qui dure au moins 2 à 3 fois plus longtemps que les autres formulations précédentes (EW, EC) grâce à la nouvelle formulation d'encapsulation du pyriproxyfène, qui est utilisé contre les parasites agricoles. L'invention concerne également l'utilisation du type CS dans la lutte contre les larves et les nymphes de moustiques, de mouches domestiques, de blattes, dans le contexte de la santé publique. La technique de fabrication d'encapsulation et l'efficacité supérieure obtenue sont dans le cadre de l'invention.
PCT/TR2016/000003 2015-01-09 2016-01-11 Technique de formulation de capsule pour le pyriproxyfène, un analogue d'hormone juvénile utilisé comme régulateur de croissance d'insectes WO2016111661A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
TR201500246 2015-01-09
TR2015/00246 2015-01-09

Publications (1)

Publication Number Publication Date
WO2016111661A1 true WO2016111661A1 (fr) 2016-07-14

Family

ID=55949053

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/TR2016/000003 WO2016111661A1 (fr) 2015-01-09 2016-01-11 Technique de formulation de capsule pour le pyriproxyfène, un analogue d'hormone juvénile utilisé comme régulateur de croissance d'insectes

Country Status (1)

Country Link
WO (1) WO2016111661A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106719677A (zh) * 2017-01-09 2017-05-31 山西奥赛诺生物科技有限公司 一种防治食用菌菇蚊的吡丙醚水乳剂、制备方法及应用

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030181453A1 (en) 2000-07-06 2003-09-25 Satoshi Nakamura Insecticides
US20050202057A1 (en) * 2004-03-01 2005-09-15 Sumitomo Chemical Company, Limited Insect growth regulating composition
JP2007063181A (ja) * 2005-08-31 2007-03-15 Sumitomo Chemical Co Ltd 水性懸濁状組成物
CN101379982B (zh) 2008-07-17 2012-09-26 张少武 一种含有吡丙醚和阿维菌素的杀虫组合物
CN103385251A (zh) 2012-05-12 2013-11-13 陕西韦尔奇作物保护有限公司 一种含吡丙醚的杀虫组合物
CN103783036A (zh) * 2013-11-20 2014-05-14 深圳诺普信农化股份有限公司 含有吡丙醚微胶囊的杀虫剂水悬浮剂及其制备方法

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030181453A1 (en) 2000-07-06 2003-09-25 Satoshi Nakamura Insecticides
US20050202057A1 (en) * 2004-03-01 2005-09-15 Sumitomo Chemical Company, Limited Insect growth regulating composition
JP2007063181A (ja) * 2005-08-31 2007-03-15 Sumitomo Chemical Co Ltd 水性懸濁状組成物
CN101379982B (zh) 2008-07-17 2012-09-26 张少武 一种含有吡丙醚和阿维菌素的杀虫组合物
CN103385251A (zh) 2012-05-12 2013-11-13 陕西韦尔奇作物保护有限公司 一种含吡丙醚的杀虫组合物
CN103783036A (zh) * 2013-11-20 2014-05-14 深圳诺普信农化股份有限公司 含有吡丙醚微胶囊的杀虫剂水悬浮剂及其制备方法

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 200729, Derwent World Patents Index; AN 2007-297287, XP002758355 *
DATABASE WPI Week 201452, Derwent World Patents Index; AN 2014-N12037, XP002758356 *
DAVID J SCHUSTER ET AL: "Novel Formulations of Microencapsulated Essential Oils and IGRs for the Management of Silverleaf Whitefly and TYLCV on Agricultural Crops", 4 November 2008 (2008-11-04), pages 1 - 3, XP055277322, Retrieved from the Internet <URL:http://www.botanocap.com/images/PDFs/FloridaPaper.PDF> [retrieved on 20160602] *
SCHWARTZ L ET AL: "Controlled-release systems for the insect growth regulator pyriproxyfen", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 51, no. 20, 24 September 2003 (2003-09-24), pages 5985 - 5989, XP002344990, ISSN: 0021-8561, DOI: 10.1021/JF0342472 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106719677A (zh) * 2017-01-09 2017-05-31 山西奥赛诺生物科技有限公司 一种防治食用菌菇蚊的吡丙醚水乳剂、制备方法及应用

Similar Documents

Publication Publication Date Title
JP6882241B2 (ja) 殺有害生物剤のスプレードリフトを制御するためのマイクロカプセル化油
BR112016023564B1 (pt) Processo de produção de microcápsulas e método de controle de fungos fitopatogênicos
CN107836461A (zh) 环保型农药乳油
EP3809845B1 (fr) Co-formulation stable de benzoylurée avec des pyréthroïdes
CN105557747A (zh) 一种稳定型农药微囊悬浮剂
CN108432751A (zh) 一种农药微囊悬浮剂及其制备方法和应用
MX2013009264A (es) Formulacion estable.
US8901037B2 (en) Composition having a germination-preventing activity, processes for obtaining said compositions and use thereof
CN102204529A (zh) 一种噻唑磷微胶囊悬浮剂及其制备方法
CN100594790C (zh) 鱼藤酮与抗生素杀菌剂混配农药制剂
WO2016111661A1 (fr) Technique de formulation de capsule pour le pyriproxyfène, un analogue d&#39;hormone juvénile utilisé comme régulateur de croissance d&#39;insectes
CN106305735A (zh) 一种含有噁霉灵和吲唑磺菌胺的杀菌组合物
JP6790063B2 (ja) トリアゾール殺菌剤、脂肪酸アミド及び芳香族炭化水素を含む、乳剤
CN104585230A (zh) 一种含有噻唑膦与氟吡菌酰胺的杀线虫组合物
CN102805089A (zh) 一种含丁氟螨酯和甲氨基阿维菌素的杀虫杀螨组合物
US20140100196A1 (en) Phytosanitary microemulsion and the procedure for obtaining it
WO2017061959A1 (fr) Composition pesticide comprenant une combinaison de molécules de bifenthrine et d&#39;abamectine sous forme de gélule
JP2021123581A (ja) マイクロカプセル農薬組成物
CN101194613B (zh) 鱼藤酮与吡蚜酮混配农药制剂
CN104970021A (zh) 一种含有喹啉铜与辛菌胺醋酸盐的杀菌组合物
CN104304259B (zh) 一种包括吡氟酰草胺与胺唑草酮的混合除草剂及制备方法
CN105076146A (zh) 一种含有高效氟吡甲禾灵与苯嘧磺草胺的除草组合物
CN101213971B (zh) 鱼藤酮与茚虫威混配农药制剂
CN108271792A (zh) 一种含有异恶唑草酮与吡氟酰草胺的除草组合物
CN101194615B (zh) 鱼藤酮与抑食肼混配农药制剂

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 16721265

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 16721265

Country of ref document: EP

Kind code of ref document: A1